Diddy is poised to release his 5th studio album in September of this year, titled “Off The Grid – Vol. 1”. Will his newest contributions resonate on Billboard’s Charts? Let’s take a look at all 5 times he reached the #1 spot on Billboard’s Hot 100 Chart.
All #1 Songs With Diddy That Reached #1

Even though Diddy (P. Diddy, Puff Daddy, Puffy, Sean Combs) actually hit the charts 37 times, 15 of them made the top 10. But, sometimes to get to the top, you need some assistance. Ever the Master Collaborator, these are the 5 times Diddy made it to the top of the heap. Here we go.
1 – I’LL BE MISSING YOU (Puff Daddy and Faith Evans featuring 112)
Hitting the top of the charts on June 14, 1997, I’ll Be Missing You stayed on the charts for 33 weeks.
Fueled by the death of B.I.G., Diddy joined forces with Big’s ex, Faith Evans (and girl group 112), and came up with a super hit song. Of course, sampling the ultra favorite “Every Breath You Take” by the Police didn’t hurt either.
2 – MO MONEY, MO PROBLEMS (The Notorious B.I.G. featuring Puff Daddy and Mase)
August 30, 1997, was the date that Mo Money, Mo Problems reached the top of the Billboard Hot 100 Chart. The Notorious B.I. G.’s song charted for 30 weeks.
3 – SHAKE YOUR TAIL FEATHER (Nelly, P. Diddy and Murphy Lee)
On September 6, 2003, Shake Your Tail Feather held that coveted #1 spot on Billboard. 30 weeks was how long this song by Nelly, Diddy and Murphy Lee remained on the charts.
4 – CAN’T NOBODY HOLD ME DOWN (Puff Daddy featuring Mase)

With the help of Mase, Can’t Nobody Hold Me Down reached #1 on March 22, 1997. The charts saw this contribution on its charts for 28 weeks.
5 – BUMP BUMP BUMP (B2K featuring Diddy)
Reaching the prized #1 position on Billboard, Bump, Bump Bump with B2K charted for 22 weeks.
Although every time Diddy hit the #1 position on Billboard’s Hot 100 Chart, he was always with another artist. Can he do it solo? Time will tell, the rappers new music entry will drop in September.
For more Entertainment News check us out at drenchedinblack.com. It’s your brand new destination for hot, black celebrity news.